4-Methylmorpholine → HCID 59363835, compound

HRID 1430648Notes

Reaction equation

HRID 1430648 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1)([CH3:9])[C:6]([OH:8])=O.[CH3:25][O:26][C:27](=[O:36])[CH2:28][C:29]1[N:30]=[C:31]([NH2:35])[S:32][C:33]=1[Cl:34].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CN1CCOCC1>C(Cl)Cl>[CH3:25][O:26][C:27](=[O:36])[CH2:28][C:29]1[N:30]=[C:31]([NH:35][C:6](=[O:8])[C:5]([O:4][C:3]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:2]=2[F:1])([C:10]2[CH:11]=[CH:12][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:14][CH:15]=2)[CH3:9])[S:32][C:33]=1[Cl:34]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59363828HCID 59363828, compoundHCID 72221007HCID 72221007, compound

Product 1

HCID 59363835HCID 59363835, compoundYield 250.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-(2,4-Difluoro-phenoxy)-2-(4-methanesulfonyl-phenyl)-propionic acid (0.110 g, 0.22 mmol), (2-Amino-5-chloro-thiazol-4-yl)-acetic acid methyl ester (0.071 g, 0.32 mmol), HOBt (0.052 g, 0.38 mmol), and EDCI (0.074 g, 0.38 mmol) in methylene dichloride (10 ml) was added N-methylmorpholine (0.039 g, 0.38 mmol). The resulting mixture was stirred at room temperature for overnight followed by dilution with 10 ml methylene dichloride. The reaction mixture was poured onto water (20 ml), and organic layer separated, washed with water (2×20 ml), brine (20 ml), dried over sodium sulfate and solvent evaporated to get residue which was purified by preparative TLC using 50% ethyl acetate in hexane as mobile. To give desired compound (0.30 g). 1H NMR (400 MHz, CDCl3): δ 1.45 (t, J=7.2 Hz, 3H), 1.93 (s, 3H), 3.14 (s, 3H), 3.77 (d, J=2.8 Hz, 1H), 4.26 (q, J=7.2 Hz, 1H), 6.69-6.77 (m, 2H), 6.96-7.02 (m, 1H), 7.89 (d, J=8.4 Hz, 2H), 8.07 (d, J=8.4 Hz, 1H); MS (D) m/z: 559.00 (M+1).

Workup

  1. additionThe reaction mixture was poured onto water (20 ml), and organic layer
  2. customseparated
  3. washwashed with water (2×20 ml), brine (20 ml)
  4. dry with materialdried over sodium sulfate and solvent
  5. customevaporated
  6. customto get residue which
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-0171cb11de6e40a3b880320a3a0f223e
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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